WO2022253681A1 - Procédé de désacétylation, compositions et leurs utilisations - Google Patents

Procédé de désacétylation, compositions et leurs utilisations Download PDF

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Publication number
WO2022253681A1
WO2022253681A1 PCT/EP2022/064274 EP2022064274W WO2022253681A1 WO 2022253681 A1 WO2022253681 A1 WO 2022253681A1 EP 2022064274 W EP2022064274 W EP 2022064274W WO 2022253681 A1 WO2022253681 A1 WO 2022253681A1
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WIPO (PCT)
Prior art keywords
flavor
composition
ppm
modifying
weight
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PCT/EP2022/064274
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English (en)
Inventor
Eric Frerot
Alexandre Philippe NELL
Robert Wagner
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Firmenich Sa
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Publication date
Application filed by Firmenich Sa filed Critical Firmenich Sa
Priority to CN202280029947.8A priority Critical patent/CN117255622A/zh
Priority to EP22731144.6A priority patent/EP4301158A1/fr
Priority to BR112023022013A priority patent/BR112023022013A2/pt
Publication of WO2022253681A1 publication Critical patent/WO2022253681A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/201—Compounds of unspecified constitution characterised by the chemical reaction for their preparation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2026—Hydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids

Definitions

  • the disclosure relates to a process for deacetylating certain acetyl-containing compounds, as well as the compositions formed from the process.
  • the acetyl-containing compounds are acetyl-containing compounds derived from avocado.
  • the disclosure also provides uses of the deacetylated compositions to enhance salty taste, umami taste, or kokumi taste.
  • the disclosure provides ingestible compositions that include the deacetylated compositions and one or more of a salty tastant, an umami tastant, or a kokumi tastant.
  • the disclosure provides methods of reducing or eliminating the amount of one or more of a salty tastant, an umami tastant, or a kokumi tastant by incorporating such deacetylated compositions into an ingestible composition. In some other aspects, the disclosure provides uses of the deacetylated compositions to mask a bitter taste.
  • the taste system provides sensory information about the chemical composition of the external world.
  • Taste transduction is one of the more sophisticated forms of chemically triggered sensation in animals. Signaling of taste is found throughout the animal kingdom, from simple metazoans to the most complex of vertebrates. Mammals are believed to have five basic taste modalities: sweet, bitter, sour, salty, and umami. .
  • Salty, umami tastes as well as kokumi sensation are most commonly associated with the savory tastes, such as that found in meat products, cheeses, tomatoes, mushrooms, soy sauce, fish sauce, miso, fermented products, and the like. Mammals generally perceive such tastes to be a pleasurable sensation. Many of these typical sources of these tastes are high in salt (sodium chloride), glutamates, or other compounds believed to be unhealthy if ingested in high quantities.
  • hypertension is a condition in which the pressure of the blood against artery walls is high enough that it may eventually cause heart disease and other health problems.
  • Excessive sodium intake also adversely affect the balance of water and minerals in the body. For example, excessive sodium intake can cause calcium loss, which can lead to osteoporosis and other problems.
  • Excessive consumption of food products containing glutamates can also have certain adverse health effects, as glutamates may interfere with the functioning of neurotransmitters. Thus, it is generally desirable to reduce the consumption of salt and glutamates.
  • animal -derived ingredients such as animal- derived fats, meat products, or dairy products, which also impart savory taste.
  • Enhancement of salt, umami, or kokumi flavors provides an alternative approach to partially or completely replacing ingredients that are traditionally used to impart such tastes. Even so, there are few compounds, especially naturally derived compounds, that can accomplish this effectively. Thus, there is a continuing need to discover new compounds having utility as flavor modifiers, especially compounds that enhance, among other flavors, the taste of salt, umami, kokumi, or any combination thereof.
  • the present disclosure relates to a deacetylation process that produces, among other things, natural avocado triols that can be used effectively to enhance the taste of salt, umami, kokumi, or any combination thereof, or, in certain instances, to mask a bitter taste.
  • the disclosure provides a process for deacetylating avocado acetates, the process comprising:
  • the disclosure provides a flavor-modifying composition, which is formed by the process of the first aspect, or any embodiments thereof.
  • the disclosure provides flavor-modifying compositions comprising (2R,4R)- 1,2, 4-trihydroxy - heptadec-16-ene.
  • the flavor-modifying composition further comprises (2R,4R)-l,2,4-trihydroxyheptadec-16-yne.
  • the disclosure provides uses of the flavor-modifying composition of the second aspect, or any related aspects.
  • the disclosure provides corresponding methods of using the flavor-modifying compounds of the second aspect, or any related aspects, the method comprising introducing the flavor-modifying composition to an ingestible composition, such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying composition of the second aspect, or any related aspects, to modify a flavor of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor modifying composition of the second aspect, or any related aspects, to modify the flavor of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying composition of the second aspect, or any related aspects, to enhance a salty taste of an ingestible composition.
  • the disclosure provides uses of the flavor-modifying composition of the second aspect, or any related aspects, to reduce the salt (e.g., sodium chloride) content of an ingestible composition.
  • the disclosure provides corresponding methods of using any flavor-modifying compositions of the second aspect, or any related aspects, to enhance a salty taste of an ingestible composition, the method comprising introducing the flavor modifying compositions to an ingestible composition.
  • the ingestible composition comprises a salty tastant, such as sodium chloride, potassium chloride, or any combination thereof.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying composition of the second aspect, or any related aspects, to enhance an umami taste of an ingestible composition.
  • the disclosure provides uses of the flavor-modifying composition of the second aspect, or any related aspects, to reduce or eliminate the glutamate or aspartate content of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying composition of the second aspect, or any related aspects, to enhance an umami taste of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is free or substantially free (for example, no more than 1000 ppm) of monosodium glutamate (MSG).
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to enhance a kokumi taste of an ingestible composition.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to reduce or eliminate glutamyl (e.g., L-glutamyl peptides) content of an ingestible composition.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to reduce or eliminate animal (e.g., animal broth or meat) content of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying composition of the second aspect, or any related aspects, to enhance a kokumi taste of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to mask a bitter taste of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying composition of the second aspect, or any related aspects, to mask a bitter taste of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to enhance a perceived sweetness of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying composition of the second aspect, or any related aspects, to enhance a perceived sweetness of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to enhance a perceived juiciness of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying composition of the second aspect, or any related aspects, to enhance a perceived juiciness of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to enhance a perceived fat content of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying composition of the second aspect, or any related aspects, to enhance a perceived fat content of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the disclosure provides uses of the flavor- modifying composition of the second aspect, or related aspects, to reduce the fat content of an ingestible composition.
  • the disclosure provides methods of reducing the fat content of an ingestible composition, the method comprising introducing the flavor-modifying composition of the second aspect to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to enhance a perceived animal product content of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor- modifying composition of the second aspect, or any related aspects, to enhance a perceived animal product content of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the disclosure provides uses of the flavor- modifying composition of the second aspect, or related aspects, to reduce the animal product content of an ingestible composition.
  • the disclosure provides methods of reducing the animal product content of an ingestible composition, the method comprising introducing the flavor modifying composition of the second aspect to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to enhance a perceived alcohol content of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying composition of the second aspect, or any related aspects, to enhance a perceived alcohol content of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the ingestible content is a low- alcohol or zero- alcohol beverage.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to enhance mouthfeel of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying composition of the second aspect, or any related aspects, to enhance mouthfeel an ingestible composition, the method comprising introducing the flavor modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions of the second aspect, or any related aspects, to reduce the perception of an off note of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying composition of the second aspect, or any related aspects, to reduce a perception of an off note an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the off note is a note characteristic of plant proteins, such as pea proteins, including a cereal note, a cardboard note, a green note, a pungent note, an astringent note, or any combination thereof.
  • the disclosure provides ingestible compositions comprising the flavor-modifying composition of the second aspect, or any related aspects.
  • concentration of the compound of formula (II) in the ingestible composition ranges from 0.1 ppm to 1000 ppm, or from 0.5 ppm to 500 ppm.
  • the ingestible composition comprises a salty tastant, an um ami tastant, a kokumi tastant, a bitter tastant, or any combination thereof.
  • the disclosure provides flavored products comprising the ingestible composition of the sixteenth aspect, or any embodiments thereof.
  • the flavored products are beverage products, such as soda, flavored water, tea, broth, and the like.
  • the flavored products are food products, such as yogurt, soup, and the like.
  • the flavored product is a meat analogue product or a dairy analogue product.
  • the flavored product is a seafood analogue product, such as an analogue of fish, shrimp, crab, scallops, and the like.
  • the flavored product is a meat or seafood product or meat- like product, such as a reformed meat or seafood product, including, but not limited to, ham, sausages, hot dogs, imitation crab meat, kamaboko, and canned meat or seafood products.
  • FIG. 1 shows a process scheme for the deacetylation process described herein, wherein R 1 , R 2 , and R 3 are independently a hydrogen atom or -C(0)-CH 3 , and at least one of R 1 , R 2 , and R 3 is -C(0)-CH 3 , and R 4 is C 13-17 alkyl, C 13-17 alkenyl, or C 13-17 alkynyl.
  • C a to C t> or “C a-b ” in which “a” and “b” are integers, refer to the number of carbon atoms in the specified group. That is, the group can contain from “a” to “b”, inclusive, carbon atoms.
  • a “Ci to C 4 alkyl” or “C M alkyl” group refers to all alkyl groups having from 1 to 4 carbons, that is, CH 3 -, CH 3 CH 2 -, CH 3 CH 2 CH 2 -, (CH 3 ) 2 CH-, CH3CH2CH2CH2-, CH 3 CH 2 CH(CH 3 )- and (CH 3 ) 3 C-.
  • alkyl means a straight or branched hydrocarbon chain that is fully saturated (i.e., contains no double or triple bonds).
  • an alkyl group has 1 to 20 carbon atoms (whenever it appears herein, a numerical range such as “1 to 20” refers to each integer in the given range; e.g., “1 to 20 carbon atoms” means that the alkyl group may consist of 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 20 carbon atoms, although the present definition also covers the occurrence of the term “alkyl” where no numerical range is designated).
  • the alkyl group may also be a medium size alkyl having 1 to 9 carbon atoms.
  • the alkyl group could also be a lower alkyl having 1 to 4 carbon atoms.
  • the alkyl group may be designated as “Ci-4 alkyl” or similar designations.
  • “Ci-4 alkyl” indicates that there are one to four carbon atoms in the alkyl chain, i.e., the alkyl chain is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec -butyl, and t-butyl.
  • alkyl groups include, but are in no way limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, pentyl, hexyl, and the like.
  • alkyl refers to a group that is not further substituted.
  • the terms “butyl,” “pentyl,” “hexyl,” and the like refer to straight-chain moieties (and do not encompass branched-chain moieties), unless otherwise indicated to the contrary.
  • alkenyl means a straight or branched hydrocarbon chain containing one or more double bonds.
  • the alkenyl group has from 2 to 20 carbon atoms, although the present definition also covers the occurrence of the term “alkenyl” where no numerical range is designated.
  • the alkenyl group may also be a medium size alkenyl having 2 to 9 carbon atoms.
  • the alkenyl group could also be a lower alkenyl having 2 to 4 carbon atoms.
  • the alkenyl group may be designated as “C2-4 alkenyl” or similar designations.
  • C2-4 alkenyl indicates that there are two to four carbon atoms in the alkenyl chain, i.e., the alkenyl chain is selected from the group consisting of ethenyl, propen- 1-yl, propen-2-yl, propen-3-yl, buten-l-yl, buten-2-yl, buten-3-yl, buten- 4-yl, 1 -methyl -propen- 1-yl, 2-methyl -propen- 1-yl, 1-ethyl-ethen-l-yl, 2-methyl-propen-3-yl, buta-l,3-dienyl, buta-l,2,-dienyl, and buta-l,2-dien-4-yl.
  • alkenyl groups include, but are in no way limited to, ethenyl, propenyl, butenyl, pentenyl, and hexenyl, and the like. Unless indicated to the contrary, the term “alkenyl” refers to a group that is not further substituted.
  • alkynyl means a straight or branched hydrocarbon chain containing one or more triple bonds.
  • the alkynyl group has from 2 to 20 carbon atoms, although the present definition also covers the occurrence of the term “alkynyl” where no numerical range is designated.
  • the alkynyl group may also be a medium size alkynyl having 2 to 9 carbon atoms.
  • the alkynyl group could also be a lower alkynyl having 2 to 4 carbon atoms.
  • the alkynyl group may be designated as “C2-4 alkynyl” or similar designations.
  • C2-4 alkynyl indicates that there are two to four carbon atoms in the alkynyl chain, i.e., the alkynyl chain is selected from the group consisting of ethynyl, propyn-l-yl, propyn-2-yl, butyn-l-yl, butyn-3-yl, butyn-4-yl, and 2-butynyl.
  • Typical alkynyl groups include, but are in no way limited to, ethynyl, propynyl, butynyl, pentynyl, and hexynyl, and the like.
  • alkynyl refers to a group that is not further substituted.
  • radical naming conventions can include either a mono-radical or a di-radical, depending on the context.
  • a substituent requires two points of attachment to the rest of the molecule, it is understood that the substituent is a di-radical.
  • a substituent identified as alkyl that requires two points of attachment includes di-radicals such as -CH2-, -CH2CH2-, -CH2CH(CH3)CH2-, and the like.
  • a squiggly bond adjacent to a carbon-carbon double bond indicates that the substituents around the carbon-carbon double bond may connect in either an E or Z configuration, or a combination of molecules in either configuration.
  • “comprise” or “comprises” or “comprising” or “comprised of’ refer to groups that are open, meaning that the group can include additional members in addition to those expressly recited.
  • the phrase, “comprises A” means that A must be present, but that other members can be present too.
  • the terms “include,” “have,” and “composed of’ and their grammatical variants have the same meaning.
  • “consist of’ or “consists of’ or “consisting of’ refer to groups that are closed.
  • the phrase “consists of A” means that A and only A is present.
  • “optionally” means that the subsequently described event(s) may or may not occur. In some embodiments, the optional event does not occur. In some other embodiments, the optional event does occur one or more times.
  • a or B is to be given its broadest reasonable interpretation, and is not to be limited to an either/or construction.
  • the phrase “comprising A or B” means that A can be present and not B, or that B is present and not A, or that A and B are both present.
  • A for example, defines a class that can have multiple members, e.g., Ai and A2, then one or more members of the class can be present concurrently.
  • substituents or linking groups having only a single atom may be referred to by the name of the atom.
  • substituent “-H” may be referred to as “hydrogen” or “a hydrogen atom”
  • substituent “-F” may be referred to as “fluorine” or “a fluorine atom”
  • the linking group “-0-” may be referred to as “oxygen” or “an oxygen atom.”
  • Points of attachment for groups are generally indicated by a terminal dash (-) or by an asterisk (*).
  • a group such as *-CH 2 -CH 3 or -CH 2 -CH 3 both represent an ethyl group.
  • Chemical structures are often shown using the “skeletal” format, such that carbon atoms are not explicitly shown, and hydrogen atoms attached to carbon atoms are omitted entirely.
  • the structure /A/ represents butane (i.e., n-butane).
  • aromatic groups such as benzene, are represented by showing one of the contributing resonance structures.
  • salty tastant is a compound that, when ingested, (i) elicits or enhances a perception of salty taste alone or in the presence of a salt, such as sodium chloride or (ii) alters the flow of ions through one or more ion channel associated with perception of salty taste.
  • ion channels associated with the perception of salty taste include the ENaC channel, the TrpV 1 channel and the TrpML3 channel.
  • the term “enhance salty taste” refers to increasing the perception of the presence of a salty tastant, while directly contributing only secondarily (or not at all) to salty taste.
  • an “umami tastant” is a compound that, when ingested, (i) elicits or enhances a perception of an umami taste alone or in the presence of another umami tastant or (ii) activates the T1R umami taste receptor.
  • the term “enhance umami taste” refers to increasing the perception of the presence of an umami tastant, while directly contributing only secondarily (or not at all) to umami taste.
  • bitter tastant is a compound that, when ingested, (i) elicits or enhances a perception of a bitter taste alone or in the presence of another bitter tastant or (ii) activates one or more T2R bitter taste receptors.
  • mask bitter taste refers to decreasing the perception of the presence of a bitter tastant.
  • a “kokumi tastant” is a compound that, when ingested, elicits or enhances a perception of a kokumi taste alone or in the presence of another kokumi tastant.
  • the kokumi taste is the taste typically associated with gamma-glutamyl tripeptides, fermented foods, and the like.
  • the term “enhance kokumi taste” refers to increasing the perception of the presence of a kokumi tastant, while directly contributing only secondarily (or not at all) to kokumi taste.
  • juiciness refers to the presence of liquids, such as water and liquid fat, within a product.
  • the term “enhance perceived juiciness” refers to increasing the perception of the presence of liquid within a product without actually increasing the amount of liquid in the product. For example, compounds that induce increased saliva production can enhance the perception of juiciness.
  • fattiness refers to the presence of fatty acid glycerides (for example, triglycerides) within a product.
  • impaired fattiness refers to increasing the perception of the presence of fatty acid glycerides within a product without actually increasing the amount of fatty acid glycerides in the product.
  • alcohol refers to ethanol, when used in the context of describing an ingredient of a food or beverage product.
  • a “pungent tastant” or a “spicy tastant” is a compound that, when ingested, activates the TRpV 1 receptor and thereby elicits or enhances a perception of a pungent taste or a spicy taste. Examples of such compounds include capsaicin and the pungent ingredients in mustard and wasabi.
  • the term “reduce pungent taste” or “reduce spicy taste” refers to decreasing the perception of the presence of a pungent tastant or a spicy tastant.
  • the disclosure provides a process for deacetylating acetates, the process comprising: (a) providing a starting composition comprising one or more avocado acetate compounds of formula (I) wherein R 1 , R 2 , and R 3 are independently a hydrogen atom or -C(0)-CH 3 , and at least one of R 1 , R 2 , and R 3 is -C(0)-CH 3 , and R 4 is C 13-17 alkyl, C 13-17 alkenyl, or C 13-17 alkynyl; and (b) introducing water, an organic acid, and an organic alcohol to the starting composition to hydrolyze the one or more avocado acetate compounds and form a product composition comprising one or more triol compounds of formula (II)
  • R 1 , R 2 , and R 3 can have any suitable value, as long as one of them is -C(0)-CH3.
  • R 1 and R 3 are a hydrogen atom, and R 2 is -C(0)-CH3.
  • R 1 and R 2 are a hydrogen atom, and R 3 is - C(0)-CH 3 .
  • R 1 is a hydrogen atom, and R 2 and R 3 are both -C(0)-CH 3 .
  • all three of R 1 , R 2 , and R 3 are -C(0)-CH 3 .
  • variable R 4 can have any suitable value consistent with the definition set forth above.
  • the avocado acetate compounds of formula (I) comprise acetates of avocadene (acetates of (2R,4R)-l,2,4-trihydroxyheptadec-16-ene) and acetates of avocadyne (acetates of (2R,4R)-l,2,4-trihydroxyheptadec-16-yne).
  • the resulting triols of formula (II) comprise avocadene ((2R,4R)-l,2,4-trihydroxyheptadec-16-ene) and avocadyne ((2R,4R)-l,2,4-trihydroxy- heptadec - 16-yne) .
  • the disclosure provides a process for increasing avocado triol content, the process comprising: (a) providing a starting composition comprising avocadene, avocadyne, one or more avocadene acetates, and one or more avocadyne acetates; and (b) introducing water, an organic acid, and an organic alcohol to the starting composition to hydrolyze a portion of the one or more avocadene acetates and a portion of the avocadyne acetates to form avocadene and avocadyne, respectively.
  • the starting composition can be derived from any suitable source.
  • the starting composition comprises oil extracted from avocado, for example, the fruit of the Persea americana tree. Such oil can be alternatively referred to as “avocado oil.”
  • the avocado oil is filtered or otherwise processed to remove residual non-fatty material, such as cellulosic materials.
  • the starting composition comprises at least 50% by weight, or at least 60% by weight, or at least 70% by weight, or at least 80% by weight, or at least 90% by weight, or at least 95% by weight, or at least 97% by weight, or at least 99% by weight, of avocado oil, based on the total weight of the starting composition.
  • the starting composition comprises an amount of triol compounds of formula (II).
  • the starting material comprises an avocado oil fraction.
  • the fraction may be formed by any suitable means of fractionating seed oils.
  • the avocado oil fraction comprises an elevated concentration of one or more compounds of formula (I), according to any of the embodiments set forth above, relative to unfractionated avocado oil.
  • the starting composition comprises at least 50% by weight, or at least 60% by weight, or at least 70% by weight, or at least 80% by weight, or at least 90% by weight, or at least 95% by weight, or at least 97% by weight, or at least 99% by weight, of an avocado oil fraction, based on the total weight of the starting composition.
  • the starting composition comprises avocado oil and one or more avocado oil fractions.
  • the starting composition comprises at least 50% by weight, or at least 60% by weight, or at least 70% by weight, or at least 80% by weight, or at least 90% by weight, or at least 95% by weight, or at least 97% by weight, or at least 99% by weight, of an avocado oil and one or more avocado oil fractions, based on the total weight of the starting composition.
  • the starting composition comprises one or more avocado acetate compounds of formula (I).
  • the avocado acetate compounds are naturally present in the avocado oil.
  • the avocado acetate compounds are added to the starting composition, so as to increase the concentration of such compounds in the starting composition compared to their concentration in the avocado oil. The concentration of such compounds may vary from batch to batch for avocado oil.
  • the deacetylation process disclosed herein comprises introducing water, an organic acid, and an organic alcohol to the starting composition to hydrolyze the one or more avocado acetate compounds and form a product composition comprising one or more triol compounds of formula (II), or any embodiments thereof.
  • any form of water can be used in the process. In some embodiments, however, the water is distilled water or deionized water. Any suitable amount of water can be used relative to the amount of avocado oil and/or avocado oil fraction in the starting composition. In some embodiments, the weight ratio of the water introduced to the avocado oil and/or avocado oil fraction ranges from 2:1 to 12:1, or from 3:1 to 10:1.
  • any suitable organic acids can be used in the process.
  • the organic acid is citric acid, oxalic acid, malonic acid, malic acid, tartaric acid, or any combination thereof.
  • the organic acid is citric acid.
  • Any suitable amount of the organic acid can be used relative to the amount of avocado oil and/or avocado oil fraction in the starting composition.
  • the weight ratio of the organic acid introduced to the avocado oil and/or avocado oil fraction ranges from 1:3 to 3:1, or from 1:2 to 2:1.
  • any suitable organic alcohols can be used in the process.
  • the organic alcohol is a water-miscible alcohol.
  • the organic alcohol is methanol, ethanol, isopropanol, or any combination thereof.
  • the organic alcohol is ethanol.
  • Any suitable amount of the organic alcohol can be used relative to the amount of avocado oil and/or avocado oil fraction in the starting composition.
  • the weight ratio of the organic alcohol introduced to the avocado oil and/or avocado oil fraction ranges from 3:1 to 20:1, or from 6:1 to 18:1.
  • the deacetylation reaction is typically carried out with the application of heat for a period of time.
  • the reaction mixture is heated to a temperature of at least 60 °C, or at least 70 °C, or at least 80 °C, and no greater than 100 °C, or no greater than 95 °C, or no greater than 90 °C.
  • the heat can be applied for any suitable period of time. In some embodiments, the heat is applied for a period ranging from 6 hours to 48 hours, or from 12 hours to 36 hours.
  • the heat is applied at a temperature and for a time to cause the evaporation of much of the organic alcohol and a portion of the water to form a concentrated product composition.
  • a concentrated product composition For example, in some embodiments, at least 90% by weight, or at least 95% by weight, of the organic alcohol is evaporated.
  • the evaporation results in a two-phase system, with the organic phase containing most, if not nearly all, of the desired triol compounds of formula (II).
  • the resulting organic phase can be separated from the aqueous phase of the concentrated product composition and subjected to one or more washings.
  • washings can be carried out with water, or with an aqueous base solution, such as an aqueous carbonate solution.
  • At least a portion of the optionally washed organic phase of the concentrated product composition is fractionated to isolate a fraction comprising a higher concentration of triol compounds of formula (II), namely an enriched product composition.
  • the fractionating can be carried out by methods known in the art, such as through crystallization, extraction, chromatography, and the like. In some embodiments, the fractionation is carried out by chromatography using standard organic solvents.
  • the enriched product composition can contain any suitable concentration of compounds of formula (II).
  • the enriched product composition comprises at least 20% by weight, or at least 30% by weight, or at least 40% by weight, or at least 50% by weight, of compounds of formula (II), based on the total weight of the enriched product composition.
  • the process can result in any suitable conversion of the acetate compounds of formula (I) to the triol compounds of formula (II).
  • at least 30% by weight, or at least 40% by weight, or at least 50% by weight, or at least 60% by weight, or at least 70% by weight, or at least 80% by weight, or at least 90% by weight, of the acetate compounds of formula (I) are converted (and recovered) to triol compounds of formula (II).
  • the product composition or enriched product composition has a relatively low concentration of avocado acetates of formula (I).
  • the product composition or enriched product composition comprises no more than 25% by weight, or no more than 20% by weight, or no more than 15% by weight, or no more than 10% by weight, or no more than 5% by weight, of avocado acetates of formula (I).
  • Isotopes may be present in the compounds described. Each chemical element as represented in a compound structure may include any isotope of said element.
  • a hydrogen atom may be explicitly disclosed or understood to be present in the compound.
  • the hydrogen atom can be any isotope of hydrogen, including but not limited to hydrogen-1 (protium) and hydrogen-2 (deuterium).
  • reference herein to a compound encompasses all potential isotopic forms unless the context clearly dictates otherwise.
  • compositions produced by the processes described above have utility as flavor modifying compositions, for example, for enhancing certain tastes, such as salty taste, umami taste, kokumi taste, and the like.
  • such flavor-modifying compositions comprise one or more triol compounds of formula (II).
  • triol compounds can make up any suitable concentration in the flavor- modifying composition.
  • the flavor-modifying compositions comprise at least 30% by weight, or at least 40% by weight, or at least 50% by weight, or at least 60% by weight, or at least 70% by weight, or at least 80% by weight, or at least 90% by weight, of triol compounds of formula (II).
  • the flavor- modifying compositions comprise avocadene ((2R,4R)-l,2,4-trihydroxyheptadec-16-ene) and avocadyne ((2R,4R)-l,2,4-trihydroxy- heptadec-16-yne).
  • the avocadene and avocadyne can be present in any suitable ratio relative to each other.
  • the weight ratio of avocadene to avocadyne in the flavor- modifying composition ranges from 1:2 to 5:1, or from 1:1 to 3:1.
  • Avocadene and avocadyne may make up any suitable concentration in the flavor modifying composition.
  • the avocadene and avocadyne collectively, make up at least 10% by weight, or at least 15% by weight, or at least 20% by weight, or at least 25% by weight, or at least 30% by weight, or at least 35% by weight, or at least 40% by weight, of the flavor-modifying composition.
  • the flavor-modifying compositions can also include other triol compounds of formula (II).
  • Such other triol compounds include, but are not limited to, the following:
  • Such additional triols can be present in the flavor-modifying composition in any suitable concentration depending, for example, on the natural concentration of their acetates in the starting composition.
  • the disclosure provides uses and methods of using the flavor modifying compositions (in any form according to the preceding aspects and embodiments thereof).
  • the disclosure provides uses of the flavor-modifying compositions set forth above, for example in a food or beverage product.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above, the method comprising introducing the flavor-modifying composition to an ingestible composition, such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to modify a flavor of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to modify the flavor of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to enhance a salty taste of an ingestible composition.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to reduce the salt (e.g., sodium chloride) content of an ingestible composition.
  • the disclosure provides corresponding methods of using any flavor-modifying compositions set forth above to enhance a salty taste of an ingestible composition, the method comprising introducing the flavor-modifying compositions to an ingestible composition.
  • the ingestible composition comprises a salty tastant, such as sodium chloride, potassium chloride, or any combination thereof.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the introduction or use of the flavor-modifying compositions permits reduction of the salty tastant (e.g., sodium chloride) by at least 10%, or at least 20%, or at least 30%, or at least 40%, or at least 50%, or at least 60%, or at least 70%, or at least 80%, or at least 90%.
  • the salty tastant e.g., sodium chloride
  • the disclosure provides uses of the flavor-modifying compositions set forth above to enhance an um ami taste of an ingestible composition.
  • the disclosure provides uses of the flavor-modifying composition of the second aspect, or any related aspects, to reduce or eliminate an umami tastant (e.g., glutamate or aspartate) content of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to enhance an umami taste of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is free or substantially free (for example, contains no more than 1000 ppm, or no more than 900 ppm, or no more than 800 ppm, or no more than 700 ppm, or no more than 600 ppm, or no more than 500 ppm, or no more than 400 ppm, or no more than 300 ppm, or no more than 200 ppm, or no more than 100 ppm) of monosodium glutamate (MSG).
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to enhance a kokumi taste of an ingestible composition.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to reduce or eliminate glutamyl (e.g., L-glutamyl tripeptides) content of an ingestible composition.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to reduce or eliminate animal (e.g., animal broth or meat) content of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to enhance a kokumi taste of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to mask a bitter taste of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to mask a bitter taste of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the ingestible composition comprises a bitter tastant, such as potassium chloride.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to enhance a perceived sweetness of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to enhance a perceived sweetness of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to reduce a pungent or spicy taste of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to reduce a pungent or spicy taste of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition. Such reduction occurs through binding to the TRpV 1 receptor and reducing its response to compounds that activate the receptor.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the ingestible composition comprises a pungent tastant or a spicy tastant, such as capsaicin and vanilloids in pungent foods, such as mustard, horseradish, and wasabi.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to enhance a perceived juiciness of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to enhance a perceived juiciness of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to enhance a perceived fat content of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to enhance a perceived fat content of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to reduce the fat content of an ingestible composition.
  • the disclosure provides methods of reducing the fat content of an ingestible composition, the method comprising introducing the flavor-modifying compositions set forth above to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the ingestible composition comprises one or more non-animal-derived fats, such as cocoa butter.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to enhance a perceived animal product content of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor modifying compositions set forth above to enhance a perceived animal product content of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to reduce or eliminate the animal product content of an ingestible composition.
  • the disclosure provides methods of reducing or eliminating the animal product content of an ingestible composition, the method comprising introducing the flavor-modifying compositions set forth above to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the flavored product is a meat analogue product.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to enhance a perceived alcohol content of an ingestible composition (for example, among other things, by activating certain heat receptors).
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to enhance a perceived alcohol content of an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the ingestible content is a low-alcohol or zero- alcohol beverage, such as a hard seltzer product.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to enhance mouthfeel of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to enhance mouthfeel an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the disclosure provides uses of the flavor-modifying compositions set forth above to reduce the perception of an off note of an ingestible composition.
  • the disclosure provides corresponding methods of using the flavor-modifying compositions set forth above to reduce a perception of an off note an ingestible composition, the method comprising introducing the flavor-modifying composition to an ingestible composition.
  • the ingestible composition is a flavored product such as a flavored food or beverage product.
  • the off note is a note characteristic of plant proteins, such as pea proteins, including a cereal note, a cardboard note, a green note, a pungent note, an astringent note, or any combination thereof.
  • the foregoing uses and methods generally involve the use or introduction of the flavor-modifying composition to an ingestible composition having one or more additional components or ingredients.
  • the disclosure provides ingestible compositions comprising any flavor-modifying compositions of the foregoing aspects or embodiments thereof.
  • the ingestible compositions can include the flavor-modifying compositions (according to any of the embodiments set forth above) in any suitable concentration.
  • the flavor-modifying compositions are present in an amount sufficient to enhance a taste (e.g., enhance an umami, enhance a kokumi, or enhance a salty taste of the ingestible composition.
  • the ingestible composition comprises the flavor-modifying compositions in a concentration of no greater than 1000 ppm, or no greater than 900 ppm, or no greater than 800 ppm, or no greater than 700 ppm, or no greater than 600 ppm, or no greater than 500 ppm, or no greater than 400 ppm, or no greater than 300 ppm, or no greater than 200 ppm, or no greater than 150 ppm, or no greater than 100 ppm, or no greater than 50 ppm, or no greater than 40 ppm, or no greater than 30 ppm, or no greater than 20 ppm, or no greater than 10 ppm.
  • the flavor-modifying composition is present in a minimum amount, such as 0.1 ppm, 0.5 ppm, or 1 ppm.
  • the ingestible composition comprises the flavor-modifying composition in a concentration ranging from 1 ppm to 1000 ppm, or 1 ppm to 900 ppm, or 1 ppm to 800 ppm, or 1 ppm to 700 ppm, or 1 ppm to 600 ppm, or 1 ppm to 500 ppm, or 1 ppm to 400 ppm, or 1 ppm to 300 ppm, or 1 ppm to 200 ppm, or from 1 ppm to 150 ppm, or from 1 ppm to 100 ppm, or from 1 ppm to 50 ppm, or from 1 ppm to 40 ppm, or from 1 ppm to 30 ppm, or from 1 ppm to 20 ppm, or from 0.5 ppm to 1000 ppm, or from 0.5 ppm.
  • the ingestible composition comprises a salty tastant and a flavor-modifying composition (according to any of the embodiments set forth above).
  • the salty tastant is sodium chloride, potassium chloride, or a combination thereof.
  • the salty tastant is sodium chloride.
  • the salty tastant is potassium chloride.
  • the ingestible composition comprises the salty tastant at a lower concentration than an equally salty-tasting composition not comprising the flavor modifying composition (according to any of the embodiments set forth above).
  • the concentration of the salty tastants is more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less, or more than 80% less, or more than 90% less than the concentration of salty tastants in an equally salty-tasting composition not comprising the flavor-modifying composition (according to any of the embodiments set forth above).
  • the salty tastant is present in the ingestible composition at a concentration ranging from 0.001 percent by weight to 1.0 percent by weight, or from 0.001 percent by weight to 0.9 percent by weight, or from 0.001 percent by weight to 0.8 percent by weight, or from 0.001 percent by weight to 0.7 percent by weight, or from 0.001 percent by weight to 0.6 percent by weight, or from 0.001 percent by weight to 0.5 percent by weight, or from 0.001 percent by weight to 0.4 percent by weight, or from 0.001 percent by weight to 0.3 percent by weight, or from 0.001 percent by weight to 0.2 percent by weight, or from 0.001 percent by weight to 0.1 percent by weight, or from 0.01 percent by weight to 1.0 percent by weight, or from 0.01 percent by weight to 0.9 percent by weight, or from 0.01 percent by weight to 0.8 percent by weight, or from 0.01 percent by weight to 0.7 percent by weight, or from 0.01 percent by weight to 0.6 percent by weight, or from 0.01 percent by weight to
  • the ingestible composition comprises an um ami tastant and the flavor-modifying composition (according to any of the embodiments set forth above).
  • the umami tastant is a glutamate, an arginate, a purine ribonucleitide, or a combination thereof.
  • the salty tastant is monosodium glutamate (MSG).
  • the umami tastant is a purine ribonucleotide (for example, inosine monophosphate (IMP), guanosine monophosphate (GMP), hypoxanthine, inosine, or any combination thereof.
  • the umami tastant is inosine monophosphate (IMP), guanosine monophosphate (GMP), or a combination thereof.
  • the ingestible composition comprises the umami tastant at a lower concentration than an equally umami - tasting composition not comprising the flavor-modifying composition (according to any of the embodiments set forth above).
  • the concentration of the umami tastants is more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less, or more than 80% less, or more than 90% less than the concentration of umami tastants in an equally umami- tasting composition not comprising the flavor-modifying composition (according to any of the embodiments set forth above).
  • the umami tastant is present in the ingestible composition at a concentration ranging from 1 ppm to 1000 ppm, or from 1 ppm to 900 ppm, or from 1 ppm to 800 ppm, or from 1 ppm to 700 ppm, or from 1 ppm to 600 ppm, or from 1 ppm to 500 ppm, or from 1 ppm to 400 ppm, or from 1 ppm to 300 ppm, or from 1 ppm to 200 ppm, or from 1 ppm to 100 ppm, or from 1 ppm to 75 ppm, or from 1 ppm to 50 ppm, or from 1 ppm to 25 ppm, or from 1 ppm to 10 ppm, based on the total weight of the ingestible composition.
  • the ingestible composition comprises no more than 10 ppm, or no more than 5 ppm, or no more than 1 ppm of monosodium glutamate, based on the total weight of the ingestible composition.
  • the ingestible composition comprises fat, such as animal or vegetable fat, and a flavor-modifying composition (according to any of the embodiments set forth above).
  • the introduction of the flavor modifying composition permits one to use less fat (such as more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less, or more than 80% less, or more than 90% less) and still achieve a level of fatty characteristic of a comparable product that employs a higher concentration of fat but not the flavor-modifying composition.
  • the use of the flavor-modifying composition permits the elimination of fat from the composition.
  • the fat can be any suitable fat, such as a fat derived from an animal or vegetable fat.
  • the fat is an animal fat, such as milk fat (including fat in various cheeses), beef fat, pork fat, poultry fat, lamb fat, goat fat, fish oil, butter, and the like.
  • the fat is a non-animal fat, such as olive oil, canola oil, corn oil, safflower oil, nut oil, peanut oil, cashew oil, soybean oil, palm oil, palm kernel oil, coconut oil, cocoa butter, and nut butters (such as peanut butter, cashew butter, almond butter, hazelnut butter, and the like).
  • the fat is cocoa butter.
  • the fat can be present in any suitable concentration in the ingestible composition.
  • the fat concentration in the ingestible composition ranges from 1 percent by weight to 60 percent by weight, or from 1 percent by weight to 50 percent by weight, or from 1 percent by weight to 40 percent by weight, or from 1 percent by weight to 30 percent by weight, or from 1 percent by weight to 20 percent by weight, or from 1 percent by weight to 10 percent by weight.
  • the ingestible composition comprises a kokumi tastant and the flavor-modifying composition (according to any of the embodiments set forth above).
  • the kokumi tastant is a yeast extract, a fermented food product, cheese, garlic or extracts thereof, a gamma-glutamyl- containing polypeptide, a gamma-glutamyl-containing oligopeptide (such as gamma- glutamyl-containing tripeptides); a flavor-modifying composition (such as a cinnamic acid amide or a derivative thereof), a nucleotide, an oligonucleotide, a plant extract, a food extract, or any combination thereof.
  • the kokumi tastant is a gamma-glutamyl- containing tripeptide.
  • the ingestible composition comprises the kokumi tastant at a lower concentration than an equally kokumi-tasting composition not comprising the flavor-modifying composition (according to any of the embodiments set forth above).
  • the concentration of the kokumi tastants is more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less, or more than 80% less, or more than 90% less than the concentration of kokumi tastants in an equally kokumi-tasting composition not comprising the flavor-modifying composition (according to any of the embodiments set forth above).
  • the kokumi tastant is present in the ingestible composition at a concentration ranging from 1 ppm to 1000 ppm, or from 1 ppm to 900 ppm, or from 1 ppm to 800 ppm, or from 1 ppm to 700 ppm, or from 1 ppm to 600 ppm, or from 1 ppm to 500 ppm, or from 1 ppm to 400 ppm, or from 1 ppm to 300 ppm, or from 1 ppm to 200 ppm, or from 1 ppm to 100 ppm, or from 1 ppm to 75 ppm, or from 1 ppm to 50 ppm, or from 1 ppm to 25 ppm, or from 1 ppm to 10 ppm, based on the total weight of the ingestible composition.
  • the ingestible composition comprises alcohol, and the flavor-modifying composition (according to any of the embodiments set forth above).
  • the introduction of the flavor- modifying composition permits one to use less alcohol (such as more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less, or more than 80% less, or more than 90% less) and still achieve a level of alcoholic characteristic of a comparable product that employs a higher concentration of alcohol but not the flavor modifying composition.
  • the use of the flavor- modifying composition permits the elimination of alcohol from the composition.
  • the alcohol can have any suitable concentration in the ingestible compositions.
  • the alcohol concentration ranges from 1 percent by volume to 50 percent by volume, or from 1 percent by volume to 45 percent by volume, or from 1 percent by volume to 40 percent by volume, or from 1 percent by volume to 35 percent by volume, or from 1 percent by volume to 30 percent by volume, or from 1 percent by volume to 25 percent by volume, or from 1 percent by volume to 20 percent by volume, or from 1 percent by volume to 15 percent by volume, or from 1 percent by volume to 10 percent by volume, or from 1 percent by volume to 5 percent by volume, based on the total volume of the ingestible composition.
  • the ingestible composition comprises no more than 1 percent by volume alcohol, based on the total volume of the ingestible composition.
  • Such ingestible compositions can be in any suitable form.
  • the ingestible composition is a food product, such as any of those specifically listed below.
  • the ingestible composition is a beverage product, such as a soda (such as a hard soda), and the like.
  • the alcohol can present in any suitable form, such as alcohol formed from grains, cane sugar, fruits, and the like.
  • ingestible compositions comprise a bitter tastant and a flavor modifying composition (according to any of the embodiments set forth above).
  • bitter tastants include, but are not limited to, active pharmaceutical ingredients (APIs), tannins (such as those in coffee, tea, or wine), ginseng, vitamins, minerals, limonin or nomelin (such as found in citrus juices), caffeine, quinine, catechins, polyphenols, potassium chloride, menthol, other commonly used oral care ingredients, cooling agents (such as N-ethyl- N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, N-(lH-pyrazol-3-yl)- N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide, 2-(4-fluorophenoxy)-N-(lH-pyrazol-3-yl)- N-(thiophen-2-ylmethyl)acetamide, 2-(4-flu
  • the flavor-modifying composition may be used in combination with such bitter tastants in any suitable ratio (w/w) ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.
  • w/w ratio
  • the ingestible composition comprises one or more sweeteners according to any of the embodiments set forth below.
  • sweeteners can be present in any suitable amount.
  • the sweetener is present in a concentration ranging from 0.1% to 12% by weight. In some embodiments, the sweetener is present in an amount from 0.2% to 10% by weight. In some embodiments, the sweetener is present in an amount from 0.3% to 8% by weight. In some embodiments, the sweetener is present in an amount from 0.4% to 6% by weight. In some embodiments, the sweetener is present in an amount from 0.5% to 5% by weight. In some embodiments, the sweetener is present in an amount from 1% to 2% by weight. In some embodiments, the sweetener is present in an amount from 0.1% to 5% by weight.
  • the sweetener is present in an amount from 0.1% to 4% by weight. In some embodiments, the sweetener is present in an amount from 0.1% to 3% by weight. In some embodiments, the sweetener is present in an amount from 0.1% to 2% by weight. In some embodiments, the sweetener is present in an amount from 0.1% to 1% by weight. In some embodiments, the sweetener is present in an amount from 0.1% to 0.5% by weight. In some embodiments, the sweetener is present in an amount from 0.5% to 10% by weight. In some embodiments, the sweetener is present in an amount from 2% to 8% by weight.
  • the sweetener is sucrose, fructose, glucose, xylitol, erythritol, or combinations thereof.
  • the percentages set forth above are weight percent, based on the total weight of the ingestible composition.
  • the sweetener is present in an amount from 10 ppm to 1000 ppm. In some embodiments, the sweetener is present in an amount from 20 ppm to 800 ppm. In some embodiments, the sweetener is present in an amount from 30 ppm to 600 ppm. In some embodiments, the sweetener is present in an amount from 40 ppm to 500 ppm. In some embodiments, the sweetener is present in an amount from 50 ppm to 400 ppm. In some embodiments, the sweetener is present in an amount from 50 ppm to 300 ppm. In some embodiments, the sweetener is present in an amount from 50 ppm to 200 ppm.
  • the sweetener is present in an amount from 50 ppm to 150 ppm.
  • the sweetener is a steviol glycoside, a mogroside, a derivative of either of the foregoing, such as glycoside derivatives (e.g., glucosylates), or any combination thereof.
  • compositions can include any suitable sweeteners or combination of sweeteners.
  • the sweetener is a common saccharide sweeteners, such as sucrose, fructose, glucose, and sweetener compositions comprising natural sugars, such as corn syrup (including high fructose corn syrup) or other syrups or sweetener concentrates derived from natural fruit and vegetable sources.
  • the sweetener is sucrose, fructose, or a combination thereof.
  • the sweetener is sucrose.
  • the sweetener is selected from rare natural sugars including D-allose, D-psicose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arbinose, D-turanose, and D-leucrose.
  • the sweetener is selected from semi-synthetic “sugar alcohol” sweeteners such as erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin, and the like.
  • the sweetener is selected from artificial sweeteners such as aspartame, saccharin, acesulfame-K, cyclamate, sucralose, and alitame.
  • the sweetener is selected from the group consisting of cyclamic acid, mogroside, tagatose, maltose, galactose, mannose, sucrose, fructose, lactose, allulose, neotame and other aspartame derivatives, glucose, D-tryptophan, glycine, maltitol, lactitol, isomalt, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolyzate (HSH), stevioside, rebaudioside A, other sweet Stevia-based glycosides, chemically modified steviol glycosides (such as glucosylated steviol glycosides), mogrosides, chemically modified mogrosides (such as glucosylated mogrosides), carrelame and other guanidine-based sweeteners.
  • HGS hydrogenated glucose syrup
  • HSH hydrogenated starch hydrolyzate
  • stevioside rebaudioside A
  • the sweetener is a combination of two or more of the sweeteners set forth in this paragraph. In some embodiments, the sweetener may combinations of two, three, four or five sweeteners as disclosed herein. In some embodiments, the sweetener may be a sugar. In some embodiments, the sweetener may be a combination of one or more sugars and other natural and artificial sweeteners. In some embodiments, the sweetener is a sugar. In some embodiments, the sugar is cane sugar. In some embodiments, the sugar is beet sugar. In some embodiments, the sugar may be sucrose, fructose, glucose or combinations thereof. In some embodiments, the sugar may be sucrose. In some embodiments, the sugar may be a combination of fructose and glucose.
  • the sweetener can also include, for example, sweetener compositions comprising one or more natural or synthetic carbohydrate, such as com syrup, high fructose corn syrup, high maltose com syrup, glucose symp, sucralose syrup, hydrogenated glucose symp (HGS), hydrogenated starch hydrolyzate (HSH), or other syrups or sweetener concentrates derived from natural fmit and vegetable sources, or semi-synthetic “sugar alcohol” sweeteners such as polyols.
  • sweetener compositions comprising one or more natural or synthetic carbohydrate, such as com syrup, high fructose corn syrup, high maltose com syrup, glucose symp, sucralose syrup, hydrogenated glucose symp (HGS), hydrogenated starch hydrolyzate (HSH), or other syrups or sweetener concentrates derived from natural fmit and vegetable sources, or semi-synthetic “sugar alcohol” sweeteners such as polyols.
  • Non-limiting examples of polyols in some embodiments include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerin), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo- oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose symp, isomaltulose, maltodextrin, and the like, and sugar alcohols or any other carbohydrates or combinations thereof capable of being reduced which do not adversely affect taste.
  • the sweetener may be a natural or synthetic sweetener that includes, but is not limited to, agave inulin, agave nectar, agave symp, amazake, brazzein, brown rice symp, coconut crystals, coconut sugars, coconut syrup, date sugar, fructans (also referred to as inulin fiber, fructo-oligosaccharides, or oligo-fructose), green stevia powder, stevia rebaudiana, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M and other sweet stevia-based glycosides, stevioside, stevioside extracts, honey, Jerusalem artichoke s
  • the sweetener can be a chemically or enzymatically modified natural high potency sweetener.
  • Modified natural high potency sweeteners include glycosylated natural high potency sweetener such as glucosyl-, galactosyl-, or fructosyl- derivatives containing 1-50 glycosidic residues.
  • Glycosylated natural high potency sweeteners may be prepared by enzymatic transglycosylation reaction catalyzed by various enzymes possessing transglycosylating activity.
  • the modified sweetener can be substituted or unsubstituted.
  • Additional sweeteners also include combinations of any two or more of any of the aforementioned sweeteners.
  • the sweetener may comprise combinations of two, three, four or five sweeteners as disclosed herein.
  • the sweetener may be a sugar.
  • the sweetener may be a combination of one or more sugars and other natural and artificial sweeteners.
  • the sweetener is a caloric sweetener, such as sucrose, fructose, xylitol, erythritol, or combinations thereof.
  • the ingestible compositions are free (or, in some embodiments) substantially free of stevia-derived sweeteners, such as steviol glycosides, glucosylated steviol glycosides, or rebaudiosides.
  • the ingestible compositions are either free of stevia-derived sweeteners or comprise stevia-derived sweeteners in a concentration of no more than 1000 ppm, or no more than 500 ppm, or no more than 200 ppm, or no more than 100 ppm, or no more than 50 ppm, or no more than 20 ppm, or no more than 10 ppm, or no more than 5 ppm, or no more than 3 ppm, or no more than 1 ppm.
  • the ingestible compositions can, in certain embodiments, comprise any additional ingredients or combination of ingredients as are commonly used in food and beverage products, including, but not limited to: acids, including, for example citric acid, phosphoric acid, ascorbic acid, sodium acid sulfate, lactic acid, or tartaric acid; bitter ingredients, including, for example caffeine, quinine, green tea, catechins, polyphenols, green robusta coffee extract, green coffee extract, potassium chloride, menthol, or proteins (such as proteins and protein isolates derived from plants, algae, or fungi); coloring agents, including, for example caramel color, Red #40, Yellow #5, Yellow #6, Blue #1, Red #3, purple carrot, black carrot juice, purple sweet potato, vegetable juice, fruit juice, beta carotene, turmeric curcumin, or titanium dioxide; preservatives, including, for example sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfate, sorbic acid, or benzoic acid; antioxidants including, for example ascorbic acid, calcium dis
  • the ingestible compositions can have any suitable pH.
  • the flavor-modifying compositions enhance the sweetness of a sweetener under a broad range of pH, e.g., from lower pH to neutral pH.
  • the lower and neutral pH includes, but is not limited to, a pH from 1.5 to 9.0, or from 2.5 to 8.5; from 3.0 to 8.0; from 3.5 to 7.5; and from 4.0 to 7.
  • compounds as disclosed and described herein, individually or in combination can enhance the perceived sweetness of a fixed concentration of a sweetener in taste tests at a compound concentration of 50 mM, 40 pM, 30 pM, 20 pM, or 10 pM at both low to neutral pH value.
  • the enhancement factor of the compounds as disclosed and described herein, individually or in combination, at the lower pH is substantially similar to the enhancement factor of the compounds at neutral pH.
  • Such consistent sweet enhancing property under a broad range of pH allow a broad use in a wide variety of foods and beverages of the compounds as disclosed and described herein, individually or in combination.
  • the ingestible compositions set forth according to any of the foregoing embodiments also include, in certain embodiments, one or more additional flavor-modifying compounds, such as compounds that enhance sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), compounds that block bitterness, compounds that enhance umami, compounds that reduce sourness or licorice taste, compounds that enhance saltiness, compounds that enhance a cooling effect, or any combinations of the foregoing.
  • additional flavor-modifying compounds such as compounds that enhance sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), compounds that block bitterness, compounds that enhance umami, compounds that reduce sourness or licorice taste, compounds that enhance saltiness, compounds that enhance a cooling effect, or any combinations of the foregoing.
  • ingestible compositions disclosed herein the flavor modifying composition is combined with one or more sweetness enhancing compounds.
  • Such sweetness enhancing compounds include, but are not limited to, 3-((4-amino-2,2-dioxo- 1 //-benzol ⁇ -
  • 2-yl)isonicotinamide 4-amino-5,6-dimethylthieno[2,3-d]pyrimidin-2(lH)-one, hesperitin dihydrochalcone, hesperitin dihydrochalcone-4’-0’glucoside, neohesperitin dihydrochalcone, naringenin, naringin, phloretin, glucosylated steviol glycosides, trilobatin, eriodictyol, homoeriodictyol, brazzein, (2R,3R)-3-acetoxy-5,7,4’-trihydroxyflavanone, (2R,3R)-
  • the flavor-modifying composition may be used in combination with such other sweetness enhancers in any suitable ratio (w/w) ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.
  • ratio ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such
  • the flavor- modifying composition is combined with glucosylated steviol glycosides in any of the above ratios.
  • glucosylated steviol glycoside refers to the product of enzymatically glucosylating natural steviol glycoside compounds. The glucosylation generally occurs through a glycosidic bond, such as an a- 1,2 bond, an a- 1,4 bond, an a- 1.6 bond, a b-1,2 bond, a b-1,4 bond, a b-1,6 bond, and so forth.
  • the flavor- modifying composition is combined with 3-((4-amino-2,2-dioxo-l//-benzo[c][l,2,6]thiadiazin-5-yl)oxy)-2,2- dimethyl-iV-propyl-propanamide, N-( 1 -((4-amino-2,2-dioxo- 1 //-benzol c
  • umami enhancing compounds include, but are not limited to, naturally derived compounds, such as (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)- acrylamide, or synthetic compounds, such as /V-(heptan-4-yl)-benzo[ ⁇ 7][l,3]dioxole- 5-carboxamide, N 1 -(2,4-dimethoxybenzyl)-N 2 -(2-(pyridin-2-yl)ethyl)-oxalamide, alkyl amides, or any other compounds set forth in U.S.
  • the flavor-modifying composition may be used in combination with such umami enhancers in any suitable ratio (w/w) ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.
  • cooling enhancing compounds include, but are not limited to, naturally derived compounds, such as menthol or analogs thereof, or synthetic compounds, such as any compounds set forth in U.S. Patent Nos. 9,394,287 and 10,421,727.
  • the flavor-modifying composition may be used in combination with such cooling enhancers in any suitable ratio (w/w) ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14,
  • the ingestible composition comprises: N-ethyl-N-(thiophen- 2-ylmethyl)-2-(p-tolyloxy)acetamide; N-(lH-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)- 2-(p-tolyloxy)acetamide; 2-(4-fluorophenoxy)-N-(lH-pyrazol-3-yl)-N-(thiophen- 2-ylmethyl)acetamide; 2-(2-hydroxy-4-methylphenoxy)-N-(lH-pyrazol-3-yl)-N-(thiophen- 2-ylmethyl)-acetamide; 2-((2,3-dihydro-lH-inden-5-yl)oxy)-N-(lH-pyrazol-3-yl)- N-(thiophen-2-ylmethyl)-acetamide; 2-((2,3-dihydro-lH-inden-5-yl)oxy)-N-(lH-pyr
  • such ingestible compositions comprise menthol or a menthol analogue.
  • such ingestible compositions are compositions for use in oral care products, such as toothpaste, mouthwash, whitening compositions, dentifrices, and the like.
  • bitterness blocking compounds include, but are not limited to 3-(l-((3,5-dimethylisoxazol-
  • the flavor-modifying composition may be used in combination with such bitterness blockers in any suitable ratio (w/w) ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.
  • ratio ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such as
  • ingestible compositions disclosed herein the flavor modifying composition is combined with one or more sour taste modulating compounds.
  • sour-taste modulating compounds include, without limitation, organic acids, such as citric acid, ascorbic acid, malonic acid, lactic acid, acetic acid, and malic acid.
  • the flavor-modifying composition may be used in combination with such sour taste modulating compounds in any suitable ratio (w/w) ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1,
  • ingestible compositions disclosed herein the flavor modifying composition is combined with one or more mouthfeel modifying compounds.
  • Such mouthfeel modifying compounds include, but are not limited to, tannins, cellulosic materials, bamboo powder, and the like.
  • the flavor- modifying composition may be used in combination with such mouthfeel enhancers in any suitable ratio (w/w) ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.
  • ingestible compositions disclosed herein the flavor modifying composition is combined with one or more flavor masking compounds.
  • flavor masking compounds include, but are not limited to, cellulosic materials, materials extracted from fungus, materials extracted from plants, citric acid, carbonic acid (or carbonates), and the like.
  • the flavor- modifying composition may be used in combination with such mouthfeel enhancers in any suitable ratio (w/w) ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1.
  • ratio ranging from 1:1000 to 1000:1, or from 1:100 to 100:1, or from, 1:50 to 50:1, or from 1:25 to 25:1, or from 1:10 to 10:1,
  • the disclosure provides uses of the flavor-modifying composition to enhance the flavor of a flavored composition, such as a flavored article.
  • flavored compositions can use any suitable flavors, such as fruit flavors, meat flavors, vegetable flavors, and the like.
  • the flavored composition is a soup or broth, a chip, a beverage, a breakfast cereal, a baked good, a meat analogue product, a meat product (such as a reformed meat product), a seafood analogue product, a seafood predict, a dairy product, or a dairy analogue product.
  • the disclosure provides flavored products comprising any compositions of the preceding aspects or embodiments thereof.
  • the flavored products are beverage products, such as soda, flavored water, tea, and the like.
  • the flavored products are food products, such as soup, meat analogues, dairy analogues, seafood analogues, meat products (such as reformed meat products, including ham, sausages, hot dogs, and canned meat products), seafood products (such as canned seafood products, imitation crab meat, fish cakes, and kamaboko), and dairy products (such as yogurt, protein drinks, and the like).
  • the beverage may be selected from the group consisting of enhanced sparkling beverages, colas, lemon-lime flavored sparkling beverages, orange flavored sparkling beverages, grape flavored sparkling beverages, strawberry flavored sparkling beverages, pineapple flavored sparkling beverages, ginger-ales, root beers, fruit juices, fruit-flavored juices, juice drinks, nectars, vegetable juices, vegetable-flavored juices, sports drinks, energy drinks, enhanced water drinks, enhanced water with vitamins, near water drinks, coconut waters, tea type drinks, coffees, cocoa drinks, beverages containing milk components, beverages containing cereal extracts and smoothies.
  • the beverage may be a soft drink.
  • the flavored product is a non-naturally-occurring product, such as a packaged food or beverage product.
  • food and beverage products or formulations include sweet coatings, frostings, or glazes for such products or any entity included in the Soup category, the Dried Processed Food category, the Beverage category, the Ready Meal category, the Canned or Preserved Food category, the Frozen Processed Food category, the Chilled Processed Food category, the Snack Food category, the Baked Goods category, the Confectionery category, the Dairy Product category, the Ice Cream category, the Meal Replacement category, the Pasta and Noodle category, and the Sauces, Dressings,
  • Condiments category the Baby Food category, the Spreads category, or the Meat category (such as reformed meats, including ham, sausages, canned meats, and the like).
  • the Soup category refers to canned/preserved, dehydrated, instant, chilled, UHT and frozen soup.
  • soup(s) means a food prepared from meat, poultry, fish, vegetables, grains, fruit and other ingredients, cooked in a liquid which may include visible pieces of some or all of these ingredients. It may be clear (as a broth) or thick (as a chowder), smooth, pureed or chunky, ready-to-serve, semi-condensed or condensed and may be served hot or cold, as a first course or as the main course of a meal or as a between meal snack (sipped like a beverage). Soup may be used as an ingredient for preparing other meal components and may range from broths (consomme) to sauces (cream or cheese-based soups).
  • the Dehydrated and Culinary Food Category usually means: (i) Cooking aid products such as: powders, granules, pastes, concentrated liquid products, including concentrated bouillon, bouillon and bouillon like products in pressed cubes, tablets or powder or granulated form, which are sold separately as a finished product or as an ingredient within a product, sauces and recipe mixes (regardless of technology); (ii) Meal solutions products such as: dehydrated and freeze dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated ready-to-cook soups, dehydrated or ambient preparations of ready- made dishes, meals and single serve entrees including pasta, potato and rice dishes; and (iii) Meal embellishment products such as: condiments, marinades, salad dressings, salad toppings, dips, breading, batter mixes, shelf stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes, including recipe mixes for salad, sold as a finished product or as an ingredient within a product, whether dehydrated, liquid
  • the Beverage category usually means beverages, beverage mixes and concentrates, including but not limited to, carbonated and non-carbonated beverages, alcoholic and non alcoholic beverages, ready to drink beverages, liquid concentrate formulations for preparing beverages such as sodas, and dry powdered beverage precursor mixes.
  • the Beverage category also includes the alcoholic drinks, the soft drinks, sports drinks, isotonic beverages, and hot drinks.
  • the alcoholic drinks include, but are not limited to beer, cider/perry, FABs, wine, and spirits.
  • the soft drinks include, but are not limited to carbonates, such as colas and non-cola carbonates; fruit juice, such as juice, nectars, juice drinks and fruit flavored drinks; bottled water, which includes sparkling water, spring water and purified/table water; functional drinks, which can be carbonated or still and include sport, energy or elixir drinks; concentrates, such as liquid and powder concentrates in ready to drink measure.
  • the drinks either hot or cold, include, but are not limited to coffee or ice coffee, such as fresh, instant, and combined coffee; tea or ice tea, such as black, green, white, oolong, and flavored tea; and other drinks including flavor-, malt- or plant-based powders, granules, blocks or tablets mixed with milk or water.
  • the Snack Food category generally refers to any food that can be a light informal meal including, but not limited to Sweet and savory snacks and snack bars.
  • snack food include, but are not limited to fruit snacks, chips/crisps, extruded snacks, tortilla/com chips, popcorn, pretzels, nuts and other sweet and savory snacks.
  • snack bars include, but are not limited to granola/muesli bars, breakfast bars, energy bars, fruit bars and other snack bars.
  • the Baked Goods category generally refers to any edible product the process of preparing which involves exposure to heat or excessive sunlight.
  • baked goods include, but are not limited to bread, buns, cookies, muffins, cereal, toaster pastries, pastries, waffles, tortillas, biscuits, pies, bagels, tarts, quiches, cake, any baked foods, and any combination thereof.
  • the Ice Cream category generally refers to frozen dessert containing cream and sugar and flavoring.
  • ice cream include, but are not limited to: impulse ice cream; take- home ice cream; frozen yoghurt and artisanal ice cream; soy, oat, bean (e.g., red bean and mung bean), and rice-based ice creams.
  • the Confectionery category generally refers to edible product that is sweet to the taste.
  • Examples of confectionery include, but are not limited to candies, gelatins, chocolate confectionery, sugar confectionery, gum, and the likes and any combination products.
  • the Meal Replacement category generally refers to any food intended to replace the normal meals, particularly for people having health or fitness concerns. Examples of meal replacement include, but are not limited to slimming products and convalescence products.
  • the Ready Meal category generally refers to any food that can be served as meal without extensive preparation or processing.
  • the ready meal includes products that have had recipe “skills” added to them by the manufacturer, resulting in a high degree of readiness, completion and convenience.
  • Examples of ready meal include, but are not limited to canned/preserved, frozen, dried, chilled ready meals; dinner mixes; frozen pizza; chilled pizza; and prepared salads.
  • the Pasta and Noodle category includes any pastas and/or noodles including, but not limited to canned, dried and chilled/fresh pasta; and plain, instant, chilled, frozen and snack noodles.
  • the Canned/Preserved Food category includes, but is not limited to canned/preserved meat and meat products, fish/seafood, vegetables, tomatoes, beans, fruit, ready meals, soup, pasta, and other canned/preserved foods.
  • the Frozen Processed Food category includes, but is not limited to frozen processed red meat, processed poultry, processed fish/seafood, processed vegetables, meat substitutes, processed potatoes, bakery products, desserts, ready meals, pizza, soup, noodles, and other frozen food.
  • the Dried Processed Food category includes, but is not limited to rice, dessert mixes, dried ready meals, dehydrated soup, instant soup, dried pasta, plain noodles, and instant noodles.
  • the Chill Processed Food category includes, but is not limited to chilled processed meats, processed fish/seafood products, lunch kits, fresh cut fruits, ready meals, pizza, prepared salads, soup, fresh pasta and noodles.
  • the Sauces, Dressings and Condiments category includes, but is not limited to tomato pastes and purees, bouillon/stock cubes, herbs and spices, monosodium glutamate (MSG), table sauces, soy based sauces, pasta sauces, wet/cooking sauces, dry sauces/powder mixes, ketchup, mayonnaise, mustard, salad dressings, vinaigrettes, dips, pickled products, and other sauces, dressings and condiments.
  • the Baby Food category includes, but is not limited to milk- or soybean-based formula; and prepared, dried and other baby food.
  • the Spreads category includes, but is not limited to jams and preserves, honey, chocolate spreads, nut based spreads, and yeast based spreads.
  • the Dairy Product category generally refers to edible product produced from mammal's milk.
  • dairy product include, but are not limited to drinking milk products, cheese, yoghurt and sour milk drinks, and other dairy products.
  • the Meat Product category generally refers to edible products produced from the muscle or organ tissue of mammals. Examples of such meat products include reformed meat products, such as ham, canned meat products, sausages, hot dogs, and the like.
  • Exemplary ingestible compositions include one or more confectioneries, chocolate confectionery, tablets, countlines, bagged selflines/softlines, boxed assortments, standard boxed assortments, twist wrapped miniatures, seasonal chocolate, chocolate with toys, alfajores, other chocolate confectionery, mints, standard mints, power mints, boiled sweets, pastilles, gums, jellies and chews, toffees, caramels and nougat, medicated confectionery, lollipops, liquorice, other sugar confectionery, bread, packaged/industrial bread, unpackaged/artisanal bread, pastries, cakes, packaged/industrial cakes, unpackaged/artisanal cakes, cookies, chocolate coated biscuits, sandwich biscuits, filled biscuits, savory biscuits and crackers, bread substitutes, breakfast cereals, rte cereals, family breakfast cereals, flakes, muesli, other cereals, children's breakfast cereals, hot cereals, ice cream, impulse ice
  • Exemplary ingestible compositions also include confectioneries, bakery products, ice creams, dairy products, sweet and savory snacks, snack bars, meal replacement products, ready meals, soups, pastas, noodles, canned foods, frozen foods, dried foods, chilled foods, oils and fats, baby foods, or spreads or a mixture thereof.
  • Exemplary ingestible compositions also include breakfast cereals, sweet beverages or solid or liquid concentrate compositions for preparing beverages, ideally so as to enable the reduction in concentration of previously known saccharide sweeteners, or artificial sweeteners.
  • the chewable composition may be gum, chewing gum, sugarized gum, sugar-free gum, functional gum, bubble gum including compounds as disclosed and described herein, individually or in combination.
  • the flavor- modifying composition as disclosed and described herein, individually or in combination may be provided in a flavoring concentrate formulation, e.g., suitable for subsequent processing to produce a ready-to-use (i.e., ready-to- serve) product.
  • a flavoring concentrate formulation it is meant a formulation which should be reconstituted with one or more diluting medium to become a ready-to-use composition.
  • ready-to-use composition is used herein interchangeably with “ingestible composition”, which denotes any substance that, either alone or together with another substance, can be taken by mouth whether intended for consumption or not.
  • the ready-to-use composition includes a composition that can be directly consumed by a human or animal.
  • the flavoring concentrate formulation is typically used by mixing with or diluted by one or more diluting medium, e.g., any consumable or ingestible ingredient or product, to impart or modify one or more flavors to the diluting medium.
  • a use process is often referred to as reconstitution.
  • the reconstitution can be conducted in a household setting or an industrial setting.
  • a frozen fruit juice concentrate can be reconstituted with water or other aqueous medium by a consumer in a kitchen to obtain the ready-to-use fruit juice beverage.
  • a soft drink syrup concentrate can be reconstituted with water or other aqueous medium by a manufacturer in large industrial scales to produce the ready-to-use soft drinks.
  • the flavoring concentrate formulation Since the flavoring concentrate formulation has the flavoring agent or flavor modifying agent in a concentration higher than the ready-to-use composition, the flavoring concentrate formulation is typically not suitable for being consumed directly without reconstitution. There are many benefits of using and producing a flavoring concentrate formulation. For example, one benefit is the reduction in weight and volume for transportation as the flavoring concentrate formulation can be reconstituted at the time of usage by the addition of suitable solvent, solid or liquid.
  • the flavored products set forth according to any of the foregoing embodiments also include, in certain embodiments, one or more additional flavor-modifying compounds, such as compounds that enhance sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), compounds that block bitterness, compounds that enhance umami, compounds that reduce sourness, compounds that enhance saltiness, compounds that enhance a cooling effect, or any combinations of the foregoing.
  • additional flavor-modifying compounds such as compounds that enhance sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), compounds that block bitterness, compounds that enhance umami, compounds that reduce sourness, compounds that enhance saltiness, compounds that enhance a cooling effect, or any combinations of the foregoing.
  • the sweetening or flavoring concentrate is a non-naturally-occurring product, such as a composition specifically manufactured for the production of a flavored product, such as food or beverage product.
  • the flavoring concentrate formulation comprises i) compounds as disclosed and described herein, individually or in combination; ii) a carrier; and iii) optionally at least one adjuvant.
  • carrier denotes a usually inactive accessory substance, such as solvents, binders, or other inert medium, which is used in combination with the present compound and one or more optional adjuvants to form the formulation.
  • water or starch can be a carrier for a flavoring concentrate formulation.
  • the carrier is the same as the diluting medium for reconstituting the flavoring concentrate formulation; and in other embodiments, the carrier is different from the diluting medium.
  • carrier includes, but is not limited to, ingestibly acceptable carrier.
  • the term “adjuvant” denotes an additive which supplements, stabilizes, maintains, or enhances the intended function or effectiveness of the active ingredient, such as the compound of the present invention.
  • the at least one adjuvant comprises one or more flavoring agents.
  • the flavoring agent may be of any flavor known to one skilled in the art or consumers, such as the flavor of chocolate, coffee, tea, mocha, French vanilla, peanut butter, chai, or combinations thereof.
  • the at least one adjuvant comprises one or more sweeteners.
  • the one or more sweeteners can be any of the sweeteners described in this application.
  • the at least one adjuvant comprises one or more ingredients selected from the group consisting of a emulsifier, a stabilizer, an antimicrobial preservative, an antioxidant, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, and combinations thereof.
  • a emulsifier emulsifier
  • stabilizers emulsifiers
  • antimicrobial preservatives antioxidants
  • the present flavoring concentrate formulation can be in a form selected from the group consisting of liquid including solution and suspension, solid, foamy material, paste, gel, cream, and a combination thereof, such as a liquid containing certain amount of solid contents.
  • the flavoring concentrate formulation is in form of a liquid including aqueous-based and nonaqueous-based.
  • the present flavoring concentrate formulation can be carbonated or non-carbonated.
  • the flavoring concentrate formulation may further comprise a freezing point depressant, nucleating agent, or both as the at least one adjuvant.
  • the freezing point depressant is an ingestibly acceptable compound or agent which can depress the freezing point of a liquid or solvent to which the compound or agent is added. That is, a liquid or solution containing the freezing point depressant has a lower freezing point than the liquid or solvent without the freezing point depressant.
  • the freezing point depressant may also lower the water activity of the flavoring concentrate formulation.
  • the examples of the freezing point depressant include, but are not limited to, carbohydrates, oils, ethyl alcohol, polyol, e.g., glycerol, and combinations thereof.
  • the nucleating agent denotes an ingestibly acceptable compound or agent which is able to facilitate nucleation.
  • the presence of nucleating agent in the flavoring concentrate formulation can improve the mouthfeel of the frozen Blushes of a frozen slush and to help maintain the physical properties and performance of the slush at freezing temperatures by increasing the number of desirable ice crystallization centers.
  • nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide, and combinations thereof.
  • the flavoring concentrate formulation is formulated to have a low water activity for extended shelf life.
  • Water activity is the ratio of the vapor pressure of water in a formulation to the vapor pressure of pure water at the same temperature.
  • the flavoring concentrate formulation has a water activity of less than about 0.85.
  • the flavoring concentrate formulation has a water activity of less than about 0.80.
  • the flavoring concentrate formulation has a water activity of less than about 0.75.
  • the flavoring concentrate formulation has the present compound in a concentration that is at least 2 times of the concentration of the compound in a ready-to- use composition. In one embodiment, the flavoring concentrate formulation has the present compound in a concentration that is at least 5 times of the concentration of the compound in a ready-to-use composition. In one embodiment, the flavoring concentrate formulation has the present compound in a concentration that is at least 10 times of the concentration of the compound in a ready-to-use composition. In one embodiment, the flavoring concentrate formulation has the present compound in a concentration that is at least 15 times of the concentration of the compound in a ready-to-use composition.
  • the flavoring concentrate formulation has the present compound in a concentration that is at least 20 times of the concentration of the compound in a ready-to-use composition. In one embodiment, the flavoring concentrate formulation has the present compound in a concentration that is at least 30 times of the concentration of the compound in a ready-to-use composition. In one embodiment, the flavoring concentrate formulation has the present compound in a concentration that is at least 40 times of the concentration of the compound in a ready-to-use composition. In one embodiment, the flavoring concentrate formulation has the present compound in a concentration that is at least 50 times of the concentration of the compound in a ready-to-use composition.
  • the flavoring concentrate formulation has the present compound in a concentration that is at least 60 times of the concentration of the compound in a ready-to-use composition. In one embodiment, the flavoring concentrate formulation has the present compound in a concentration that is up to 100 times of the concentration of the compound in a ready-to-use composition.
  • sweetening or flavoring concentrates set forth according to any of the foregoing embodiments also include, in certain embodiments, one or more additional flavor-modifying compounds, such as compounds that enhance sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), compounds that block bitterness (e.g., eriodictyol, homoeriodictyol, sterubin, and salts or glycoside derivatives thereof, as well as vanillyl lignans, e.g., matairesinol and other compounds set forth in PCT Publication No.
  • additional flavor-modifying compounds such as compounds that enhance sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), compounds that block bitterness (e.g., eriodictyol, homoeriodictyol, sterubin, and salts or glycoside derivatives thereof, as well as vani
  • WO 2012/146584 compounds that enhance umami (e.g., rubemamine, rubescenamine, (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide, and the like), compounds that reduce sourness and/or licorice taste, compounds that enhance saltiness, compounds that enhance a cooling effect, or any combinations of the foregoing.
  • umami e.g., rubemamine, rubescenamine, (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide, and the like
  • compounds that reduce sourness and/or licorice taste compounds that enhance saltiness, compounds that enhance a cooling effect, or any combinations of the foregoing.
  • the disclosure provides a packaged flavoring composition comprising: (a) a flavor-modifying composition (according to any of the embodiments set forth above); and (b) at least one bulking agent.
  • the packaged flavoring composition may take any suitable form including, but not limited to, an amorphous solid, a crystal, a powder, a tablet, a liquid, a cube, a Geneva or coating, a granulated product, an encapsulated form abound to or coated on to carriers/particles, wet or dried, or combinations thereof.
  • the packaged flavoring composition may contain further additives known to those skilled in the art. These additives include but are not limited to bubble forming agents, bulking agents, carriers, fibers, sugar alcohols, oligosaccharides, sugars, high intensity sweeteners, nutritive sweeteners, flavorings, flavor enhancers, flavor stabilizers, acidulants, anti-caking and free-flow agents.
  • flavorings may include those flavors known to the skilled person, such as natural and artificial flavors. These flavorings may be chosen from synthetic flavor oils and flavoring aromatics and/or oils, oleoresins and extracts derived from plants, leaves, flowers, fruits, and so forth, and combinations thereof.
  • Non-limiting representative flavor oils include spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, allspice, oil of sage, mace, oil of bitter almonds, and cassia oil.
  • sweetenings are artificial, natural and synthetic fruit flavors such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yazu, sudachi, and fruit essences including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, pineapple, watermelon, apricot, banana, melon, apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya and so forth.
  • fruit flavors such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yazu, sudachi, and fruit essences including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, pineapple, watermelon, apricot, banana, melon, apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya and so forth.
  • Other potential flavors include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor; a vanilla flavor; tea or coffee flavors, such as a green tea flavor, a oolong tea flavor, a tea flavor, a cocoa flavor, a chocolate flavor, and a coffee flavor; mint flavors, such as a peppermint flavor, a spearmint flavor, and a Japanese mint flavor; spicy flavors, such as an asafetida flavor, an ajowan flavor, an anise flavor, an angelica flavor, a fennel flavor, an allspice flavor, a cinnamon flavor, a camomile flavor, a mustard flavor, a cardamom flavor, a caraway flavor, a cumin flavor, a clove flavor, a pepper flavor, a coriander flavor, a sassafras flavor, a savory flavor, a Zanthoxyli Fructus flavor, a perilla flavor, a juniper berry flavor
  • flavoring agents may be used in liquid or solid form and may be used individually or in admixture.
  • Commonly used flavors include mints such as peppermint, menthol, spearmint, artificial vanilla, cinnamon derivatives, and various fruit flavors, whether employed individually or in admixture.
  • Flavors may also provide breath freshening properties, particularly the mint flavors when used in combination with cooling agents.
  • Flavors may also provide breath freshening properties, particularly the mint flavors when used in combination with cooling agents. These flavorings may be used in liquid or solid form and may be used individually or in admixture. Other useful flavorings include aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethylacetal, dihydrocarvyl acetate, eugenyl formate, p- methylamisol, and so forth may be used.
  • any flavoring or food additive such as those described in Chemicals Used in Food Processing, publication 1274, pages 63-258, by the National Academy of Sciences, may be used. This publication is incorporated herein by reference.
  • aldehyde flavorings include but are not limited to acetaldehyde (apple), benzaldehyde (cherry, almond), anisic aldehyde (licorice, anise), cinnamic aldehyde (cinnamon), citral, i.e., alpha-citral (lemon, lime), neral, i.e., beta-citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotrope, i.e., piperonal (vanilla, cream), vanillin (vanilla, cream), alpha-amyl cinnamaldehyde (spicy fruity flavors), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronellal (modifies, many types), decanal (citrus fruits), aldehyde C-8 (citrus fruits),
  • the flavoring may be employed in either liquid form and/or dried form.
  • suitable drying means such as spray drying the oil may be used.
  • the flavoring may be absorbed onto water soluble materials, such as cellulose, starch, sugar, maltodextrin, gum arabic and so forth or may be encapsulated. The actual techniques for preparing such dried forms are well-known.
  • the tabletop sweetener can be made to be similar to brown sugar.
  • compounds imparting brown notes can be added to the composition to make it taste more similar to brown sugar.
  • the flavorings may be used in many distinct physical forms well- known in the art to provide an initial burst of flavor and/or a prolonged sensation of flavor. Without being limited thereto, such physical forms include free forms, such as spray dried, powdered, beaded forms, encapsulated forms, and mixtures thereof.
  • Suitable bulking agents include, but are not limited to maltodextrin (10 DE, 18 DE, or 5 DE), com syrup solids (20 or 36 DE), sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose and cellulose derivatives, and the like, and mixtures thereof. Additionally, granulated sugar (sucrose) or other caloric sweeteners such as crystalline fructose, other carbohydrates, or sugar alcohols can be used as a bulking agent due to their provision of good content uniformity without the addition of significant calories.
  • maltodextrin 10
  • the at least one bulking agent may be a bulking agent described in U.S. Patent No. 8,993,027.
  • the at least one bulking agent may be a bulking agent described in U.S. Patent No. 6,607,771.
  • the at least one bulking agent may be a bulking agent described in U.S. Patent No. 6,932,982.
  • the tabletop sweetener composition may further comprise at least one anti-caking agent.
  • anti-caking agent and “flow agent” refer to any composition which prevents, reduces, inhibits, or suppresses the at least one sweetener from attaching, binding, or contacting to another sweetener molecule.
  • anti-caking agent may refer to any composition which assists in content uniformity and uniform dissolution.
  • Non- limiting examples of anti-caking agents include cream of tartar, calcium silicate, silicon dioxide, microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, Pa.), and tricalcium phosphate.
  • the anti caking agents are present in the tabletop sweetener composition in an amount from about 0.001 to about 3% by weight of the tabletop sweetener composition.
  • the sweetener compositions of any of the preceding aspects and embodiments thereof are encapsulated using typical means for encapsulating flavor or fragrance compounds.
  • typical means for encapsulating flavor or fragrance compounds are set forth in U.S. Patent Application Publication Nos. 2016/0235102, 2019/0082727, 2018/0369777, 2018/0103667, 2016/0346752, 2015/0164117, 2014/0056836, 2012/0027866, 2010/0172945, and 2007/0128234, as well as U.S. Patent Nos.
  • Products intended to replace or substitute meat, seafood, or dairy products often rely on various non-animal-based materials, such as fibers and proteins derived from plants, algae, or fungi, to simulate the texture and flavor of meat or dairy.
  • non-animal-based materials such as fibers and proteins derived from plants, algae, or fungi
  • plant proteins include soy proteins, pea proteins, bean proteins, grain proteins, and the like. Due to compositional differences between such plant-based materials and animal-derived materials, such as a lack of glutamate-containing proteins and glutathione, these products can lack the um ami or kokumi taste that consumers traditionally associate with meat or dairy products.
  • the disclosure provides a flavored product comprising a plant-based material (such as a plant-based starch, a plant-based protein, or a combination thereof) and a flavor-modifying composition (according to any aspects and embodiments set forth above).
  • the flavored product can include any features of combination of features set forth above for ingestible compositions that contain the flavor modifying composition.
  • the flavored product is a beverage, such as soy milk, almond milk, rice milk, oat milk, a protein drink, a meal-replacement drink, or other like product.
  • the flavored product is a meat-replacement product, such as a plant-based chicken product (such as a plant-based chicken nugget), a plant-based beef product (such as a plant-based burger), and the like.
  • the flavored product is a seafood-replacement product, such as a plant-based seafood product (such as a plant-based shrimp, a plant-based fish fillet, a plant-based scallop, a plant-based lobster, a plant-based crab, and the like).
  • the flavored product is a protein powder, a meal-replacement powder, a plant-based creamer for coffee or tea, and the like.
  • any such flavored products contain additional ingredients, and have additional features, as are typically used in the preparation and/or manufacture of such products.
  • a flavor-modifying composition (according to any of the embodiments set forth above) may be combined with other flavors and taste modifiers, and may even be encapsulated in certain materials, according to known technologies in the relevant art. Suitable concentrations of the flavor modifying composition are set forth above.
  • proteins or starches from algal or fungal sources can be used instead of or in combination with plant starches or proteins.
  • non-meat animal proteins such as dairy proteins and proteins from bone broth
  • dairy proteins and proteins from bone broth are commonly used in food products, and are also sold as the primary ingredient in certain protein powders.
  • Such proteins can impart flavors that lack the full um ami or kokumi taste that consumers desire. This is especially true for protein isolates, such as protein isolates of whey protein, collagen protein, casein proteins, and the like.
  • the present disclosure provides ingestible compositions that include non-meat animal proteins and the flavor-modifying composition (according to any aspects and embodiments set forth above).
  • the flavor-modifying composition can be present in any suitable combination, according to the embodiments set forth in the preceding sections of the present disclosure.
  • the non-meat animal protein is a bone protein, such as a collagen protein derived from the bones of an animal, such as a cow, pig, donkey, horse, chicken, duck, goat, goose, rabbit, lamb, sheep, buffalo, ostrich, camel, and the like.
  • the non-meat animal protein is a milk protein, such as a whey protein, a casein protein, or any combination thereof.
  • the milk can be the milk of any suitable animal, such as a cow, donkey, horse, sheep, buffalo, camel, and the like.
  • the flavor-modifying compositions can also be included in certain food or beverage products that include animal milk or materials derived from animal milk.
  • animal milk or materials derived from animal milk include cheeses, cheese spreads, yogurt, kefir, milk, processed dairy products, cottage cheese, sour cream, butter, and the like.
  • flavor-modifying compositions disclosed herein may be synthesized by methods described below, or by modification of these methods. Ways of modifying the methodology include, among others, temperature, solvent, reagents etc., known to those skilled in the art.
  • the mixture so obtained was characterized by UPLC/MS. It contained generally 24- 32% w/w avocadene and 10-16% avocadyne quantified using an external standard calibration.
  • the system was run using XCalibur software. Data processing was done using FreeStyle software. Integration of peaks was done using ISIS algorithm on the base peak chromatogram [200-700Da]. The parameters used were baseline window 80, area noise factor 500 and peak noise factor 10.
  • the system was composed of a Shimadzu LC-20AR high pressures binary pump (up to 20 mL/min) , a LH-40 liquid handler injector, fraction collector, a UV/VIS SPD-20A detector and a Sedere ELSD-90-LT detector .
  • the system was run using LabSolutions software.
  • XBridge BEH C18 OBD Prep Column 130A, 5pm 10 x 250 mm
  • Xselect CSH Prep Fluoro Phenyl column 5um 10 x 100 mm and they were eluted with 7ml/min of H20/ACN 0.1% formic acid in gradient mode.

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Abstract

La divulgation concerne un procédé de désacétylation de certains composés contenant un groupe acétyle, ainsi que les compositions formées à partir du procédé. Dans certains modes de réalisation, les composés contenant un groupe acétyle sont des composés contenant un groupe acétyle dérivés de l'avocat. Selon certains aspects, la divulgation concerne également des utilisations des compositions désacétylées pour améliorer le goût salé, le goût umami ou le goût kokumi. Dans certains modes de réalisation, la divulgation concerne des compositions pouvant être ingérées qui comprennent les compositions désacétylées et un ou plusieurs éléments parmi un composé donnant un goût salé, un composé donnant un goût umami, ou un composé donnant un goût kokumi par incorporation de telles compositions désacétylées dans une composition pouvant être ingérée. Selon certains autres aspects, la divulgation concerne des procédés de réduction ou d'élimination de la quantité d'un ou de plusieurs éléments parmi un composé donnant un goût salé, un composé donnant un goût umami, ou un composé donnant un goût kokumi. Selon certains autres aspects, la divulgation concerne des utilisations des compositions désacétylées pour masquer un goût amer.
PCT/EP2022/064274 2021-06-02 2022-05-25 Procédé de désacétylation, compositions et leurs utilisations WO2022253681A1 (fr)

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